Chesapeake City vacation rentals

Whatever you're seeking in a vacation, you'll find a rental in or around Chesapeake City that suits your style. Here are some of our favorites:

• Make use of handy extras like winery tours and a boat at "Water Front Retreat - Sunrise And Sunset Water Views". Located around 30 miles from Chesapeake City, this property has 3 bedrooms and good guest reviews.
• Another appealing choice is "Brand New Renovation In Historic District With 2 Parking Spots", which is around 50 miles from Chesapeake City. With 2 bedrooms, golf and a balcony, it has everything you need to keep you happy and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Chesapeake City vacation rental for you.

For a unique kind of vacation experience, book one of Vrbo's tiny house rentals in Chesapeake City. Be warned though — after you've experienced the tiny house lifestyle, the temptation to move into one of thes pint-sized digs will be hard to resist!

• You can look forward to a simpler way of living at "Annapolis Waterfront "tiny House" In Garden Setting". Amenities at this hideaway in Parole include a boat, heating and more.
• "A Serene Tiny Home Experience" in Parole is another great choice. A nearby bay and air conditioning will help make your time here more comfortable.

Those chores can wait, because weekends were made for fun. Stay in one of these weekend getaways in and around Chesapeake City and make the most of all the wonderful things to do close by:

• Spend your whirlwind escape at "Top Of The Chesapeake - Minutes From Historic Charlestown", which is around 9 miles to the northwest of central Chesapeake City. There's plenty of adventure and nature on your doorstep here. Try some kayaking and fishing or simply delight in the sights of Hart-Miller Island State Park and Historical Society of Cecil County.
• Alternatively, find your home away from home at "Riverfront Retreat With Panoramic Views And Breathtaking Sunsets". Use it as a base to unwind, or get active and try kayaking and mountain biking. When you're ready to discover more of the area, check out Elk Neck State Park and Bulle Rock Golf Course. This fantastic vacation rental is around 2 miles north of Chesapeake City.

Studio apartments are a hard act to follow when it comes to convenience, character and location. Get comfy in one of these studio apartments for rent in or near Chesapeake City and enjoy a taste of the local vibe:

• Make "Short Term Water Oriented Furnished Apartment" your home for a few days or more. This top property features amenities including towels and free WiFi.
• Alternatively, get into vacation mode at "Enjoy Breathtaking Beauty On The Chesapeake Bay", which comes with conveniences such as a fridge and an elevator.

There are lots of attractions around Chesapeake City to add to your itinerary. Feed your inner culture vulture with a visit to Mud and Metal and Lurman Woodland Theatre.

Just because you only have a day or two free doesn't mean you need to spend it in a characterless hotel. Head off on vacation but still have the home comforts you need at one of these short-term rentals in or around Chesapeake City:

• If you're eager to be close to the action, "Gorgeous Annapolis Getaway - Walk Everywhere" will be just the thing. It's within easy reach of the heart of Chesapeake City and an excellent base to check out attractions like Annapolis Bowl and Eisenhower Golf Course.
• Sleep, eat and explore your surroundings from "Charming Historic Annapolis Home With Two Off", another popular option. Walden Golf Club and Crofton Bowl should be on your must-do list when you're ready to go sightseeing.

Whether spent in a log cabin or a beach house, a romantic weekend getaway is a wonderful way to spice up your love life. Whisk your partner away for a couple of relaxing days at one of these appealing escapes in or near Chesapeake City:

• Sneak off on Friday for a few passionate nights at "Nancy’s Touch, A Waterfront Paradise". Roughly 7 miles from Chesapeake City, this place comes with plenty of nice touches, like a nearby bay and a fireplace.
• Another place where you can enjoy a few wonderful days together is "Piece Of Heaven On The Chesapeake". Around 9 miles from Chesapeake City, a fireplace and air conditioning add to the ambiance here.

Share your trip and boost your odds of having fun. Whether you're planning an action-packed getaway with your best friends or an overdue family reunion, you'll have your choice of large group vacation rentals in and around Chesapeake City:

• Providing space, comfort and privacy, you'll get your guests' tick of approval at "Top Of The Chesapeake - Minutes From Historic Charlestown". Up to 13 people can stay at this escape which has 5 bedrooms, a garden and a nearby river. You'll discover it around 9 miles to the northwest of Chesapeake City.
• Invite up to 14 of your best friends to "Dune Residence Glowe House Luisa To The Beach 200 M" and fill the place with love and laughter. This option has 7 bedrooms and is around 2 miles to the north of central Chesapeake City. It's packed with features to keep your group occupied, including a firepit and a nearby waterfront.

Of all the amenities a vacation rental can offer, a pool is without a doubt the most fun. Browse these houses for rent with a pool in or near Chesapeake City and spend your days splashing around. Just don't forget to bring your flamingo floatie:

• Make yourself comfortable at "Dune Residence Glowe House Luisa To The Beach 200 M", where your highest priority will be enjoying the pool. Amenities such as a fridge and childrens activities help make this escape a favorite with guests.
• Otherwise, unpack your bags at "Water View House In Charlestown". As well as its inviting pool, you can also make use of free toiletries and a TV.

Wondering what the weather's like in Chesapeake City? It has a humid subtropical climate, with average temperatures in summer ranging from 65 ºF to 85 ºF. If you're seeking more inspiration on where to stay in this impressive destination, use the search bar at the top of the page and adjust the filters to look through our entire range of Chesapeake City vacation rentals.

It's always more fun when you share those special memories with the folks you care about the most. Whether you're organizing a family break or spending time with close friends, we'll have a large vacation rental that's perfect for you. These are two of our best in and around Chesapeake City:

• Located about 9 miles to the northwest of Chesapeake City, "Top Of The Chesapeake - Minutes From Historic Charlestown" has 5 bedrooms and can sleep up to 13 guests. It comes with lots of amenities, including a travel crib and a dining table.
• "Dune Residence Glowe House Luisa To The Beach 200 M" is another top pick for families. It's about 2 miles to the north of Chesapeake City, has 7 bedrooms and accommodates up to 14 people. Useful amenities here include free toiletries and a TV.

If you'd like to sightsee, there are plenty of family-friendly attractions close by to add to your to-do list. National Aquarium in Baltimore, Six Flags America and Maryland Zoo are fine places to start.

Romantic retreats, work trips or adventures all on your own — a one-bedroom vacation rental is a perfect solution for all sorts of occasions. One of our options in or near Chesapeake City is sure to fit the bill:

• Check into "Short Term Water Oriented Furnished Apartment" for a couple of nights. This one-bedroom property offers guests a nearby waterfront and a water view and is not far from the heart of town.
• "Chesapeake City View Of C And D With Water Toy Parking" is another charming one-bedroom escape also not far from the center. When you're not out and about seeing your surroundings, make use of a water view, a nearby waterfront and much more.